2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-{2-[3,4,5-triacetoxy-6-(4,5,6-triacetoxy-2-acetoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-butyric acid methyl ester | 913625-19-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-{2-[3,4,5-triacetoxy-6-(4,5,6-triacetoxy-2-acetoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-butyric acid methyl ester
• CAS: 913625-19-1
• 化学式: C₄₉H₆₃N₉O₂₁S
• 分子量: 1146.15
• InChiKey: FYMBZXGAYBSFQH-AAMMTMCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  80.0
• 可旋转键数：
  24.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  403.13
• 氢给体数：
  4.0
• 氢受体数：
  29.0

反应信息

• 作为反应物：
  描述：

  2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-{2-[3,4,5-triacetoxy-6-(4,5,6-triacetoxy-2-acetoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-butyric acid methyl ester 在 吡啶 、 氢氟酸 作用下， 反应 2.0h， 以52%的产率得到2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-{2-[3,4,5-triacetoxy-6-(4,5-diacetoxy-2-acetoxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-butyric acid methyl ester
  参考文献：
  名称：

  Optimized design and synthesis of chemical dimerizer substrates for detection of glycosynthase activity via chemical complementation

  摘要：

  Glycosynthases catalyze the formation of a glycosidic bond between a glycosyl fluoride donor substrate and a glycosyl acceptor substrate with high yield, thus providing a valuable approach for the synthesis of carbohydrates and glycoconjugates. Chemical complementation can be used to link glycosynthase activity to the transcription of a reporter gene in vivo, providing a selection for the directed evolution of glycosynthase enzymes with improved properties. In this approach, glycosynthase activity is detected as covalent coupling between a small molecule disaccharide acceptor substrate and a small molecule disaccharide alpha-fluoro donor substrate. Here we report the optimized design and synthesis of these small molecule substrates. These optimized substrates are shown to give a robust, glycosynthase-dependent transcriptional read-out in the chemical complementation assay. The full synthesis and characterization of these substrates are reported for the first time. These optimized chemical dimerizer substrates should allow the potential of chemical complementation for the directed evolution of glycosynthases with diverse substrate specificities and improved properties to be fully realized. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.034
• 作为产物：
  描述：

  Acetic acid (3R,4S,5R,6R)-2,3-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4-diacetoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 吡啶 、 三乙烯二胺 、 potassium tert-butylate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-{2-[3,4,5-triacetoxy-6-(4,5,6-triacetoxy-2-acetoxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethylsulfanyl]-ethylcarbamoyl}-butyric acid methyl ester
  参考文献：
  名称：

  Optimized design and synthesis of chemical dimerizer substrates for detection of glycosynthase activity via chemical complementation

  摘要：

  Glycosynthases catalyze the formation of a glycosidic bond between a glycosyl fluoride donor substrate and a glycosyl acceptor substrate with high yield, thus providing a valuable approach for the synthesis of carbohydrates and glycoconjugates. Chemical complementation can be used to link glycosynthase activity to the transcription of a reporter gene in vivo, providing a selection for the directed evolution of glycosynthase enzymes with improved properties. In this approach, glycosynthase activity is detected as covalent coupling between a small molecule disaccharide acceptor substrate and a small molecule disaccharide alpha-fluoro donor substrate. Here we report the optimized design and synthesis of these small molecule substrates. These optimized substrates are shown to give a robust, glycosynthase-dependent transcriptional read-out in the chemical complementation assay. The full synthesis and characterization of these substrates are reported for the first time. These optimized chemical dimerizer substrates should allow the potential of chemical complementation for the directed evolution of glycosynthases with diverse substrate specificities and improved properties to be fully realized. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.034